Previously seen trips

Next departures for Windsor to Boston on August 28
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location
Train	7:49am	Windsor Station	5h 30m	1:19pm	Boston Route 128, MA
Train	12:55pm	Windsor Station	4h 9m	5:04pm	Boston Route 128, MA
Train	5:55pm	Windsor Station	5h 31m	11:26pm	South Station (Train Terminal)
Train	5:55pm	Windsor Station	5h 12m	11:07pm	Boston Route 128, MA
Train	5:55pm	Windsor Station	5h 25m	11:20pm	Back Bay Station

Get from Windsor to Boston

This route is served by train only

The journey takes about 4 hours 37 minutes and with fares starting at just R 415, it presents an excellent value for a comfortable ride.

12train per day

4h 37mAverage Duration

86 milesDistance

13kgCO₂ emissions

Train Companies

Amtrak

4.1/56,468 reviews

Staff4.7

Timeliness3.8

Cleanliness4.5

Wifi3.6

Based on 6468 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at R 415

US train companies:Amtrak, Amtrak Acela, Brightline

Frequently asked questions about traveling from Windsor, CT, US to Boston, MA, US by train

Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.

How much is the train ticket from Windsor to Boston?
The cheapest train tickets from Windsor to Boston start from R 415. The average price for this train route is around R 1 306. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the train journey from Windsor to Boston?
The average train ride duration from Windsor to Boston is 4h 37m, covering a distance of 86 miles (138 km). The quickest train can get you there in 3h 18m and is operated by Amtrak.
Which train operators service the Windsor to Boston route?
Several major train operators operate on this route with 12 trains available per day.
What is the earliest and latest departure time for the train from Windsor to Boston?
The earliest train departs from Windsor to Boston at 4:41am. And the latest train departs at 8:40pm.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

08/26

R 481

08/27

R 2 021

Today

No data

08/29

R 381

08/30

R 1 226

08/31

No data

09/01

No data

09/02

R 978

The cheapest trip from Windsor, CT, US to Boston, MA, US was searched and found on Aug 29, 2026 with a price of R 381

To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Windsor, CT, US to Boston, MA, US, as early as possible.

You can expect to pay from R 381 to R 3 412 for a train ticket from Windsor, CT, US to Boston, MA, US based on the last 2 days. You can expect to find the cheapest price for the trip at R 381 which is on 2026-08-29.